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Communication

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Green Soap: An Extraction and Saponification of Avocado Oil
Susan Sutheimer,* Jacqueline M. Caster, and Simone H. Smith
Chemistry Program, Green Mountain College, Poultney, Vermont 05764, United States
S Supporting Information
*

ABSTRACT: An introductory level green chemistry experiment is described that places a
new twist on soap-making in lab. In this experiment, oil is extracted from an avocado, after
which the oil is saponified to produce bars of green craft soap. Commonly used extraction
solvents, such as petroleum ether, methylene chloride, and hexane, are replaced with safer
ethyl acetate to extract the oil. Students find the experiment helpful in discovering the
reality of fats and oils in foods, and in becoming aware of the direct relationship between
oils in plants and soap. This experiment has been successfully carried out by students of
introductory organic chemistry lab classes, but could be used by a general chemistry or an
advanced placement high school class.

KEYWORDS: First-Year Undergraduate/General, Second-Year Undergraduate, Organic Chemistry,
Hands-On Learning/Manipulatives, Inquiry-Based/Discovery Learning, Green Chemistry, Natural Products, Solutions/Solvents

I

PRE-LAB ASSIGNMENT
The introductory material for the lab experiment includes
information about elaioplastids, the cell structures of plants that
contain the oil, and explains why isopropyl alcohol is used in
conjunction with ethyl acetate to break down cell structures. It
also explains that using ethyl acetate is a safer solvent than
those used historically for extractions. However, it challenges
students to find on their own the structures of fats, soap, and
ethyl acetate, as well as the chemical reaction for making soap,
and then to draw them by hand or by using molecular drawing
software. This inquiry-based, pre-lab exercise is meant to
reinforce the molecular theory behind the soap-making process.
Additionally, the combination of a fat extraction plus
saponification reaction during a single lab helps to exemplify
the real-world nature of soap production.

n a new twist to an old experiment, the procedure reported
herein provides an inquiry-based, real-world examination of
the process of preparing a soft, green, craft soap beginning with
the extraction of green-colored oil from an avocado using a
greener (safer) extraction solvent. As early as 1925, an article
appeared in this Journal describing the soap industry.1 By 1947,
the high school textbook “Applied Chemistry” listed a student
laboratory experiment on soap making.2 Several authors in this
Journal have described the soap-making process in detail for the
undergraduate and high school laboratory,3−6 with one
illustrating the versatility of the starting fats (solids) or oils
(liquid fats).3 All of these articles include images of chemical
structures of fats and soaps and explain the process of soap
making. Likewise, extractions using solvents are common in
introductory organic chemistry laboratories, as well as in
research and industrial laboratories. In this updated experiment,
both the oil extraction and soap-making techniques are
combined in a unique and fun way that illustrates the
connectivity between seemingly disparate industrial processes.
The experiment also encourages students to recognize the
presence of fats and oils in foods, and in becoming aware of the
direct relationship between oils in plants and soap.
The current experiment utilizes a greener solvent to extract
the oil from avocado by using the relatively less toxic solvent
ethyl acetate rather than the more commonly used chlorinated
solvents, petroleum ether, or hexane.7−9 Ethyl acetate is not
only regarded as a highly efficient solvent, but is also easily
degraded in the water and air compared to other solvents.10,11
Using a greener solvent emphasizes attention to the Principles
of Green Chemistry and to the toxicity to which many students
are unnecessarily subjected in some undergraduate laboratory
procedures.12
© XXXX American Chemical Society and
Division of Chemical Education, Inc.

METHOD FOR SOAP MAKING
Students work in pairs; the experiment requires 4 h to
complete. An avocado is peeled, the pit is removed, and the
flesh is extracted with a solution of ethyl acetate and isopropyl
alcohol. The decanted solvent containing the oil is evaporated
under the hood using a warm water bath. The oil, along with
additional solid fat (Crisco) and vegetable oil, is saponified by
mixing with aqueous NaOH. During a 20−30 min mixing time,
students build molecular models of fat and soap. Bars of soap
are cured for 4−6 weeks, during which time the saponification
reaction continues and the pH of the soap decreases from >12
to near neutral. Complete pre-lab and step-by-step instructions
are included in the Supporting Information.

A

DOI: 10.1021/acs.jchemed.5b00188
J. Chem. Educ. XXXX, XXX, XXX−XXX

G.It was fun and easy and it teaches you the basics of organic chemistry.jchemed. 492−495. J. Dueno. (3) Mabrouk. 192A−192B. Quality Opaque or Transparent Soap.4% fat by weight (Figure 1). Chem. Students reported significant satisfaction with REFERENCES (1) Preston. I never knew that avocados contained that much fat. 1998. Soapmaking. ■ ASSOCIATED CONTENT S Supporting Information * A complete lab handout including inquiry based pre-lab assignment. The pH decreases to near neutral (∼8) after curing for 4−6 weeks. Educ. 2 (11). 1947.. J. Applied Chemistry. S. Brokman. Natural Product Chemistry. Streff. Making Usable. instructions were recently added for students to build molecular models of fat and soap while waiting. Comparison of Two Fat Extraction Methods. S. additional fats are added to create approximately normalsized bars of soap. The Modern Soap Industry. the soap was allowed to cure slowly for 4−6 weeks. 6th ed. could be easily separated into two. 89 (8). L. R. pp 401−420. Figure 1. 1035−1044.edu. Chem. A lab assessment procedure indicated that students were able to conceptualize the theory behind extraction and reapply the extraction procedure during another. E. Sodium hydroxide is caustic and should be handled carefully. R. N.. Chem. Revised. minimally toxic if inhaled. Henry Holt and Co.epa. 2005. X. the two parts of this lab. J. O.. Educ.gov/iris/subst/0157. Educ. 2 h sections to accommodate other lab schedules.: New York. M. because students complained that the 20−30 min for “trace” to form could be better used.Journal of Chemical Education Communication ■ HAZARDS Eye protection and gloves should be worn throughout this procedure. The newly prepared bars of soap have a high pH (>12) due to residual NaOH. B DOI: 10. ■ DISCUSSION Avocado was chosen for its high fat content (∼14%). Green Chemistry: Theory and Practice. ■ ■ ACKNOWLEDGMENTS This work was supported by Green Mountain College through an Undergraduate Research Grant. 612−614. Notes The authors declare no competing financial interest. Mullins. but is generally not used in craft soap-making. However.ca/jmc/www/Chemweb/oldchemweb/ extractionmethods. http://www.. Chem. • I really liked the lab! It was straight forward and easy to follow and I can’t wait to see how it comes out. Three completed bars of soap and avocado oil.com/chemistry/ethyl-acetate (accessed Mar 2015).. The average amount of fat obtained was about 14 ± 3 g of avocado oil per avocado.. Wang. Their comments included • Overall I really liked this lab. so they should not be handled for some time after they are poured. 1925. Educ. (12) Anastas. J..sekab. was a reasonable substitute for other.. (5) Pohl. Q. 42 (9). Oxford University Press: New York. an example of student results and a table listing the mass of avocado flesh compared to avocado oil obtained by 10 students is included. • This lab was definitely very interesting.4−14. Ethyl acetate and isopropyl alcohol are both flammable. A laboratory hood should be used for evaporation of the solvents. Chem. consistently crafting three bars of a mild soap. Benning.5b00188 J. Steehler.. extraction and soap making. Ed.qc.acs. J. I never would have guessed it could be so simple. B. R. 1534−1537. This procedure did not use a “salting out” procedure that was commonly employed in lab exercises.1021/acs. W. (8) Bergeron. 82 (10). McGraw-Hill: New York. This material is available via the Internet at http://pubs. J. Chem. 1998. Educ. E. Educ. T.13 Rather. http://www. Chem. more open-ended experiment later in the semester. (4) JCE staff.. (6) Phanstiel.. This experiment has been used very successfully in four classes.htm (accessed Mar 2015). M. 2012. XXX. Synthesis of Exotic Soaps in the Chemistry Laboratory. • I enjoyed this lab thoroughly and thought that it was worthwhile both from an educational perspective and a hands-on learning opportunity to produce a useful substance. this lab and found the experiment helpful in recognizing the presence of fats and oils in foods. instructions. C. Finally.htm (accessed Mar 2015). and in becoming aware of the direct relationship between oils in plants and soap. This oil is both a coloring agent and a portion of the total fats used in the soapmaking process. F. 1999. 76 (2). J. P. • This particular lab was interesting as it both helped me understand the real synthesis aspects of soap and then view it in real time. http://web2. 2009. XXXX. ethyl acetate. T. ■ AUTHOR INFORMATION Corresponding Author *E-mail: sutheimers@greenmtn. (10) Ethyl Acetate. pp 29−55. 1053−1056.slc. XXX−XXX . Evaluating Sustainability: Soap versus Biodiesel Production from Plant Oils. C. Isopropyl alcohol was used in conjunction with the ethyl acetate to break down cell structures so that the oils were more easily extracted. M. S. more toxic solvents to extract avocado oil with 10 students reporting yields of 7. pp 189−195. with approximately 60 students (30 pairs) in 4 h organic chemistry labs that are almost exclusively populated by biology majors. I was able to see how you make natural soaps. (2) Wilson. 1965. Since the volume of avocado oil is relatively small. J. but are toxic if consumed. (11) Ethyl Acetate.org. The greener solvent. Warner. (7) Laboratory Manual to Accompany Chemistry in Context: Applying Chemistry to Society. 75 (5).. (9) O’Connor. Educ.

XXXX.5b00188 J. XXX.VP8bNfnF9u4 (accessed Mar 2015). C DOI: 10. Chem. Educ.soap-making-essentials. XXX−XXX . http://www.html#.jchemed. com/cold-process-soap-making.Journal of Chemical Education Communication (13) Soap Making Essentials.1021/acs.